Make sure you feel comfortable and confident in your agent before making offers.

The key is to find someone that YOU are comfortable working WITH and not just looking to sell you something.  

Currently in my area, there are a few, but they are all renting for market rate and above.I wasn't comfortable giving him a 60 notice and raising the rent $400 despite what my agent recommended.

I don't want to do this as a hobby but turn this into my career and my aggressive mindset will surely lead me down that path however I truly feel like I will not be comfortable doing this until I know I have someone I can rely on in the industry.

You can copy that letter and submit it with your offerers submitted and give the owner, hopefully, some comfort that you can close and afford his property.  

How did you get comfortable with buying out of state and how did you find the properties that were right for you?

I know it will get better once I'm comfortable and actually know what I am talking about, but in the mean time, what are some things that you do to keep yourself calm when meeting with buyers/seller/potential team members?

I have a really hard time getting comfortable.

Doesn't feel comfortable messing with it.

Without a level of comfort I am not going to move forward with the deal.